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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-16 08:06:15 UTC
Update Date2019-07-23 05:54:25 UTC
HMDB IDHMDB0010345
Secondary Accession Numbers
  • HMDB10345
Metabolite Identification
Common NameAldosterone 18-glucuronide
DescriptionAldosterone 18-glucuronide is a natural human metabolite of Aldosterone generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Data?1563861265
Synonyms
ValueSource
11beta,18-Epoxy-21-hydroxy-3,20-dioxopregn-4-en-18-yl-beta-D-glucopyranosiduronic acidHMDB
11beta,18-Epoxy-21-hydroxy-3,20-dioxopregn-4-en-18-yl-beta-delta-glucopyranosiduronic acidHMDB
Aldosterone-18-D-glucosiduronic acidHMDB
Aldosterone-18-D-glucuronosideHMDB
Aldosterone-18-delta-glucosiduronic acidHMDB
Aldosterone-18-delta-glucuronosideHMDB
Chemical FormulaC27H36O11
Average Molecular Weight536.5681
Monoisotopic Molecular Weight536.225761994
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S,14R,16R)-2-(2-hydroxyacetyl)-14-methyl-11-oxo-17-oxapentacyclo[14.2.1.0¹,⁵.0⁶,¹⁵.0⁹,¹⁴]nonadec-9-en-18-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S,14R,16R)-2-(2-hydroxyacetyl)-14-methyl-11-oxo-17-oxapentacyclo[14.2.1.0¹,⁵.0⁶,¹⁵.0⁹,¹⁴]nonadec-9-en-18-yl]oxy}oxane-2-carboxylic acid
CAS Registry Number3604-86-2
SMILES
[H][C@]12CC3(C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)O1)C(CC[C@@H]3C(=O)CO)C1CCC3=CC(=O)CC[C@]3(C)C21
InChI Identifier
InChI=1S/C27H36O11/c1-26-7-6-12(29)8-11(26)2-3-13-14-4-5-15(16(30)10-28)27(14)9-17(18(13)26)36-25(27)38-24-21(33)19(31)20(32)22(37-24)23(34)35/h8,13-15,17-22,24-25,28,31-33H,2-7,9-10H2,1H3,(H,34,35)/t13?,14?,15-,17-,18?,19+,20+,21-,22+,24+,25?,26+,27?/m1/s1
InChI KeyOMRIQCUHVVBJKI-ACOLCOCVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Oxepane
  • Cyclohexenone
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Tetrahydrofuran
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.68 g/LALOGPS
logP0.52ALOGPS
logP0.089ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area180.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.58 m³·mol⁻¹ChemAxon
Polarizability53.42 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar0-6402690000-f6883434cd9b283dd8c2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ba-3523019000-db1849d7bc6d8d89f58eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0403-0409050000-f124277ffdc08339588dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-0419010000-5fdd32f3c9923afc2b62JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uem-2988000000-8d0e0f23995861ec3cfcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-2209370000-37d0cbab92230b6865dfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3309210000-e793687d092724829b5fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9306100000-260bcd50a7d6dc1c5aabJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.0008 (0.0004-0.0021) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.0015 (0.00012-0.0030) umol/mmol creatinineAdult (>18 years old)BothHyperaldosteronism details
    UrineDetected and Quantified0.001 (0.00034-0.0022) umol/mmol creatinineAdult (>18 years old)BothHypertension details
    Associated Disorders and Diseases
    Disease References
    Hypertension
    1. Abdelhamid S, Blomer R, Hommel G, Haack D, Lewicka S, Fiegel P, Krumme B: Urinary tetrahydroaldosterone as a screening method for primary aldosteronism: a comparative study. Am J Hypertens. 2003 Jul;16(7):522-30. [PubMed:12850384 ]
    Aldosteronism
    1. Shakerdi LA, Connell JM, Fraser R, Wallace AM: Analysis of biological samples by gas chromatography-mass spectrometry without a reference standard: measurement of urinary 18-hydroxytetrahydro-11-dehydrocorticosterone excretion rate in human subjects. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 5;784(2):367-73. [PubMed:12505784 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB027497
    KNApSAcK IDNot Available
    Chemspider ID141209
    KEGG Compound IDNot Available
    BioCyc IDBeta-D-Glucuronides
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound160706
    PDB IDNot Available
    ChEBI ID88734
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General ReferencesNot Available

    Only showing the first 10 proteins. There are 18 proteins in total.

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
    Gene Name:
    UGT2B28
    Uniprot ID:
    Q9BY64
    Molecular weight:
    38742.9
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
    Gene Name:
    UGT2B4
    Uniprot ID:
    P06133
    Molecular weight:
    60512.035
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
    Gene Name:
    UGT1A4
    Uniprot ID:
    P22310
    Molecular weight:
    60024.535
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
    Gene Name:
    UGT2B7
    Uniprot ID:
    P16662
    Molecular weight:
    60720.15
    References
    1. Girard C, Barbier O, Veilleux G, El-Alfy M, Belanger A: Human uridine diphosphate-glucuronosyltransferase UGT2B7 conjugates mineralocorticoid and glucocorticoid metabolites. Endocrinology. 2003 Jun;144(6):2659-68. [PubMed:12746330 ]
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
    Gene Name:
    UGT2B15
    Uniprot ID:
    P54855
    Molecular weight:
    61035.815
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
    Gene Name:
    UGT2A1
    Uniprot ID:
    Q9Y4X1
    Molecular weight:
    60771.605
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
    Gene Name:
    UGT1A9
    Uniprot ID:
    O60656
    Molecular weight:
    59940.495
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
    Gene Name:
    UGT1A3
    Uniprot ID:
    P35503
    Molecular weight:
    60337.835
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
    Gene Name:
    UGT2B17
    Uniprot ID:
    O75795
    Molecular weight:
    61094.915

    Only showing the first 10 proteins. There are 18 proteins in total.